Abstract
This study concerned the controlled synthesis of periodic glycopolymers by reversible addition-fragmentation chain transfer (RAFT) copolymerization. To this end, maltose- and lactose-substituted vinyl ethers (MalVE and LacVE, respectively) and maltose-substituted maleimide (MalMI) were newly synthesized. RAFT copolymerization of MalVE and ethyl maleimide (EtMI) (monomer feed ratio: MalVE:EtMI = 1:1) afforded periodic glycopolymers (poly(MalVE-co-EtMI)) consisting of major parts of alternating structure (-(MalVE-EtMI)n-) and a small part of consecutive sequences of EtMI (–EtMI-EtMI-). Occurrence of the latter sequences was caused by the homopolymerizability of maleimide under the present polymerization condition, and the formation of the consecutive sequences of EtMI was successfully suppressed by varying the monomer feed ratio. RAFT copolymerization of LacVE and EtMI was also found to proceed and similarly yielded periodic glycopolymers (poly(LacVE-co-EtMI)). Moreover, RAFT copolymerization of LacVE and MalMI (monomer feed ratio: LacVE:MalMI = 1:1) was performed to give copolymers (poly(LacVE-co-MalMI)) having composition ratio of LacVE/MalMI ≈ 36/64. The resultant periodic glycopolymers poly(MalVE-co-EtMI) and poly(LacVE-co-EtMI) were subjected to lectin binding assay using concanavalin A and peanut agglutinin, exhibiting the glycocluster effect. Moreover, these glycopolymers obtained from the copolymerization of VE and MI were found to be non-cytotoxic.
Highlights
Glycosaminoglycans (GAGs) are known as physiologically active polysaccharides being ubiquitous both in the extracellular matrix and on cell surfaces, and play key roles in wide-ranging life phenomena as well as in diseases affecting mammalians [1,2,3]
To achieve the alternating structure, we focused on the copolymerization of an electron-rich ethers (VEs) and maleimide (MI) monomers having pendant unprotected carbohydrate moieties were and an electron-deficient vinyl monomers, which have been widely recognized to afford alternating newly designed by utilizing copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction copolymers via radical polymerization mechanism [19,20,21,22,23,24,25,26]
Study, we we demonstrated that the the reversible addition-fragmentation chain transfer (RAFT)
Summary
Glycosaminoglycans (GAGs) are known as physiologically active polysaccharides being ubiquitous both in the extracellular matrix and on cell surfaces, and play key roles in wide-ranging life phenomena as well as in diseases affecting mammalians [1,2,3]. From the view of structural aspect, GAGs are long, linear, unbranched, and negatively-charged polysaccharides composed of repeating disaccharide units consisting of an amino sugar and an uronic acid. GAGs are sulfated and distinguished from each other by the disaccharides structures and various sulfation patterns [1,2,3]. Polymers 2019, 11, × FOR PEER REVIEW of GAG mimics based on glycopolymers by both conventional and controlled polymerizations haverepeating been reported [4,5,6,7,8,9,10]. The last sugar decade, the remarkable development in disaccharide units consisting ofinan amino andwith an uronic acid. Major precisely controlled radical polymerization such as ATRP and
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